DE2202471A1 - New esters - Google Patents

Description

D-. F. Γ: -: vi-i: i: -:, - η-

f ι. : c: -. :. ':. ·. ο ι ra 8 Munich 2, ßi juhiusifraßa 4 / HI

C a s e 5 - 7 3 6 5 / A ΡΤ / l -ι -? / =

New esters

The present invention relates to new triazolylcarbaiaates their manufacture and use for pest control. The Tri azolylcarbc'imate correspond to the formula

N (I)

R - Ν— —N _ ο - O 1 Λ π | ΐ C. C. C.

wherein R _{1 is} hydrogen, alkyl or cycloalkyl, R ^ is hydrogen, alkyl or the groups -COOR ,, -CO-N (R ₃ ) CR ^) or -CN, R _{3 is} hydrogen, alkyl, alkenyl or alkynyl, R, alkyl, Alkenyl, alkynyl, alkoxy, cycloalkyl or phenyl and R _n and R, together with the nitrogen atom to which they are attached, represent a heterocyclic radical

The ones for R ,, R «, R ^> and R, possible alkoxy, alkyl, alkenyl and alkynyl chains contain 1 to 18, respectively. 2 to IB fbei the alkenyl resp. Alkiny 1 residues), but preferably 1 to 4 rcsp. 2 to 4, carbon atoms. These residues can be branched "or straight-chain, be unsubstituted or substituted. Examples of such Residues include methyl, mothoxy, tri f 1 uorir.ethyl, ethyl, etho;: v, Cynnathyl, propyl, isopropyl n-, i-, sec-, tert-butyl, allyl, Crotonyl, methallyl, propargyl or n-butynyl.

20 9 8 Λ 1/1172

The cycloalkyl radicals Dir R, and R ^, have 3 to 7, preferably 5 or 6, Ringgl i or. The fMr R, into consideration comirer: - The phenyl radical can be unsubstituted or substituted.

The substituents on the alkoxy, alkyl, alkenyl, alkynyl and phenyl radicals can be of the first or second order. Under First-order substituents are electron donors which act to increase basicity to understand. The following groups, among others, come into consideration here: halogen atoms, such as fluorine, chlorine, bromine or iodine; Alkoxy and alkylthio groups having 1 to 4 carbon atoms which are branched or can be unbranched, and are preferably unbranched and have 1 to 2 carbon atoms; lower alkoxyalkyl and Alkyl groups, where the definitions given above also apply here- * meet; r> rim. , sec. and tert. Amino groups, with lower alkyl and alkanol groups are preferred substituents; Hydroxyl and mercapto groups. The phenyl radical can also be replaced by alkyl, tr.ono- and di-haloalkyl group may be substituted.

Second order substituents include acidifying c'c Understanding electron acceptors. The following are among others Groups under consideration: Nitro and cyano groups: trilalogcnalky 1 groups, in which halogen is preferably F or Cl: lower Alkyl sulfinyl, lower alkyl sulfonyl groups, which have a ve ^ v / ee or unbranched alkyl radical having 1 to 4, preferably an unbranched alkyl radical having] or 2 carbons; Sulfamyl and su] famido groups where the amino groups are one or two Substituents, preferably a straight-chain or branched one Have an alkyl radical with 1 to 4 carbon atoms.

Compounds of the formula are of particular importance

R, - Ν --Ν

|| o _R

COC- NC " ⁷ (H)

v> rin R is hydrogen, C ₁ -C 6 alkyl, or C ₃ -C ₇ . Cycloalkyl, R ^ I. hydrogen, C, -C, alkyl or the groups -COOR, -, - CO-NC R ₇ > ^s ' ^K p>' R. Hydrogen or C -C, alkyl and R _g Cj -C, alkyl, C ₁ -C, alkoxy denote phenyl.

2 0 9 8 U 1/1 17 2

In the foreground, compounds of the formula ClI) have the following formula:

- O - C - N

^K 12

wherein R _Q C, -C, alkyl, cyclopentyl or cyclohexyl, R, "hydrogen, Cj-C, alkyl or the groups -COOCH3, -COOC ₂ H ₅ or

x ^CH 3
-CON ^, R ₁₁ hydrogen, methyl or ethyl and R ₁₂ methyl,

Mean ethyl, methoxy or phenyl.

Examples of compounds of formula (III) are i.a.

The compounds of the formula I can be prepared according to per se Methods can be produced by, for example, a) a hydroxy-triazole of the formula

R ₁ -NN

-2-LJ- «

with a carbamyl halide of the formula

Shark - C - N (V)

or
0 Ro

Shark - C - N (VI)

reacts in the presence of an acid-binding agent or

b) a salt of a hydroxy-triazole of the formula (IV) with a Carbamy] halide of the formula (V) or (VI) reacts or

c) a hydroxy-triazole of the formula (IV) is reacted with phosgene and the intermediate product with a "connection of the formula

209841/1 172

HN ^ ³ (VII) or ^H 2 ^N ~ ^R 3 <" ^VI11 )

⁴ or H ₂ NR ₄ (IX) can react.

In the formulas (IV) to CdO, the symbols R, to R, the meaning given for formula 1. Hai stands for F, Cl, Br or I, but especially for Cl or Br.

Suitable salts of hydroxytriazoles of the formula (IV) for the process according to the invention are, for example, monovalent salts Metals, in particular the alkali metal salts such as sodium or Potassium salts.

The following bases, for example, can be used as acid-binding agents: tertiary amines, such as triethylamine, dimethylaniline, Pyridine, pyridine bases; inorganic bases such as hydroxides and carbonates of alkali and alkaline earth metals are preferred Sodium and potassium carbonate.

It is recommended that the reaction be carried out in inert solvents to undertake. For example, the following are suitable for this: aromatic hydrocarbons, such as benzene, toluene, xylenes, benzines, Chlorobenzene, polychlorobenzenes, brombersDl; chlorinated alkanes with 1 to 3 carbon atoms; Ethers such as dioxane or tetrahydrofuran; Esters, such as ethyl acetate; Ketones, such as aoion, methyl ethyl ketone, Diethyl ketone.

Some of the starting materials of the formula (IV) are known Links. You can use known methods, for example by reacting an appropriately substituted semicarbazide with orthoformic acid esters getting produced.

The compounds of the formula I have a broad biocidal action and can be used to combat various types of vegetable and animal pests and used as growth regulators.

In particular, the compounds of the formula I have insecticidal properties and can be used against all stages of development such as e.g. Eggs, larvae, pupae, nymphs and adults are used by various insects. Examples of such pests are insects of the families Teltigonidae, Gryllidae., Gryllotalpidae, Blattidae,

209841/1172

Peduviidae, Phyrrohocoriae, Cimicidae, De] phacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Derreestidae, Coccinellidae, Tenebrionidae, Chryscme] idae, Bruchidae, Tineidae, Noctindae, Lymatriidae, Pyralidac, Culcidae, Tipulidae, StomoxycJae, Trypetidae, Mnscidae, Calliphoridae and Pulicidae.

The insecticidal effect can be significantly broadened by adding other insecticides and given the circumstances adjust.

The following active ingredients are suitable as additives:

209841/1172

/ 1 -

Organic phosphorus compounds

Bis-O, O-diethylphosphoric anhydride (TEPP) 2202471

Dimethyl (2,2,2-trichloro-l-hydroxyethyl) phosphonate (TRICHLORFON) ' ^ά

1,2-dibromo-2,2-dichloroethyidimethylphosphate (NALED) 2,2-dichlorovinyldimethylphosphate (DICHLORPHOS) 2-methoxycarbamyl-l-methylyinyl diiethyl phosphate (MEVINPHOS) diniethyl-l-methyl-2- (methylcarbairoyl) vinyl phosphate c \ sTOP_HOSPHATE S-fDiirethoxyphosphinyloxyJ-NN-dicethyl-cis-crotonauid (DICROTOPHOS) 2-Ch 1 οΓο-2-diet hy 1 carbamoy I -1 -me thy 1 ν i ny 1 ei i me thy 1 phosphate (PHOSPHAM I DON) O , 0-diethyl-O (or S) -2- (ethylthio) -äthyIthiophosphat (OEMElON) S-EthyIthioäthy 1-0,0-dinethy 1-dithiophosphat (IH 1OMf] (JN) OjO-diethyl-S-äthylmercaptouethyldithiophosphat (PIIORmercaptouethyldithiophosphat ) O, O-diethyl-S-2-ethylthioiethyl dithiophosphate (0ISULFO] ON) O, O-diniethyl-S-2- (ethylsulfinyl) ethylthiophosphate (OXYDEMETONMETHYL) 0,0-dimethyl-S- (1,2-dicarbethoxyethyl d (MALATHION) 6,0,0,0-tetraethyl-S, S ^f -methyIen-bis-dithiophosphate (ETHION) O-ethy 1-S, Sd i propy1 dtthiophosphat

OO-Dimethyl-S-CN-methyl-N-formylcarbamoylmethyl) -dithiophosphate (FORMOTHION) 0,0-Dimethyl-S- (N -raethylcarbamoylE! Ethy]) dithiophosphate (DIMETHOAT) 0,0-Dimethyl I-0 -pn i tropheny1thiophosphate (PARATHlON-MElHYL) 0,0-diethyl-Op-nitropheny] thiophosphate (PARATHION) 0-ethyl-0-p-nitropheny1 phenylthiophosphonate (EPN) 0,0-dimethyl-0- (4-nitro-m -tolyl thiophosphate (FEN ITROTHION) 0,0-Diiaethyl-0-2,4-5-trichlorophenyIthiophosphat (RONNEL) O-Ethy1-0,2,4,5-trichlorophenylethylthiophosphonate (TRICHLORONATE) 0,0-Dinethyl-0-2, 5-dichlorombronphenylthiophosphate (BROMOPHOS) 0,0-Din: ethyl-0- (2,5-dichloro-A-iodophenyl) -thiophosphate (IODOFENPHOS) 4-tert-buty 1-2-chloropheny 1-N-ir. ethyl-O-methylamidophosphate (CRUFOMAT) OjO-dimethyl-OO-methyl-i-methyl rercaptophenyte) thiophosphate (FENTHION) isopropyl riino-O-ethy lOf ^ -methy linercapto-3-raethylphenyl) -phosphate 0,0-diethyl-op- (methylsulfinyDphenyl thiophosphate (FENSULFOTHION) Op- {DimethyIsulfamido) pheny 1 0-, 0-dirr.ethyI thiophosphite (FAMPHtIR) 0,0, Ο ', Ο'-Te tramethyl-0,0'-thiodi-p-phenylenethiophosphate O-Ethy1-S-pheny1-ethyldi thiophosphonate
0.0-0 intet hy 1 -O-ία — m ethy I benzy i -3-hydroxyc rot onyl! Phosphate 2-chloro -] - (2,4-dichlorophenyl) vinyl diethyl phosphate (CHLORFENVINPHOS) 2-Ch1 or- 1- (2,4,5-trichiorphenyl) vinyl) -dimethylphosphate 0- [2-ChI or-1 - (2,5-dichloropheny l'jlviny 1-0,0-diethyl thiophosphate Pheny1glyoxy1onitriloxiB-O, O- diethyithiophosphate (PHOXIM) OO-diethyl-OO-chloM-methyl-Z-oxo ^ -Hl-benzopyran-T-yD-thiophosphate (COUMAPHOS) 2,3-p-dioxanedithiol-5, S-bis (0,0-diethyldithiophosphate ) (DIOXATHIONE) 5 - [(6-chloro-2-oxo-3-benzoxazolinyl) methyl] 0,0-diethyldithiophosphate (PHOSELON) 2- (diethoxyphosphinyl iciino) -1,3 -d ΐ thiolane

0,0-Dimethyl-S- [2-methoxy-1,3,4-thiadiazol-5- (4H) -onyl- / 4) -ntethyl] di thiophosphate 0,0-dimethyl-S-rphthalimidomethyl-dithiophosphate (IMIDAN) O, O-diethyl O- (3,5,6-trichloro-2-pyridyl thiophosphate 0,0-diethyl-0-2-pyrazinylthiophosphate (THIONAZINE) 0,0-diethyl-0- (2-isopropyl-4-methyl-6-pyrimidyl-thiophosphate (01AZINON) 0.0-0 diethyl-0- (2-quinoxalylithiophosphate

O _f O-dimethyl-S- (4-oxo -], 2 _t 3-benzotriazine-3 (4H) -ylniethyl) -dithiophosphate (AZINPHOSMETHYL) 0,0-diethyl-S- (4-oxo-1,2, 3-benzotriazine-3 (4H) -ylmethyl) -dithiophosphate (AZINPHOSAETHYL) S- [d, 6-diamino-s-triazin-2-yl) methyl] -0,0-dimethyldithiophosphate (BENAZON) 0,0-dimethyl -0- (3-chloro-4-nitropheny1ithiophosphate (CHLORTHIONE) O, 0-dimethyl-O (or S) -2- (ethylthioethylithiophosphate (DEMETON-S-METHYL) 2- (0,0-Dimeihy 1 -phosphory 1-thiomethy 1) -5-nethoxy-pyrone-4-3,4-di ch 1 orben zy 1 - tri phenyl phosphonige hl or id 0,0-diethyl-S- (2,5-dichlorophenylthiomethyl) dithiophosphate (ΡΗΕΝΚΛΡΤΟΝ )

2098A1 / 1172

0 _f 0-0i-ethyl-0- (A- «ethyl-cuBarinyl-7) -thiophosphate (POTASAN) 2202471

5-A _B ino-bis (dinethylaaido) phosphinyl-3-phenyl-1,2, Mriazol (TR I AMI PHOS)

N-methyl-5- (0,0-di-ethylthiolphosphoryl) -3-thiavaleraiiid (VAM1D0THI0N)

0,0-diethyl-0- [2-d? NethylaBiino-4-iiethylpyri «idyl- (6)] thiophosphate (DlOCTHYL)

O.O-Diaethyi-S-UethylcarbanoylaethylMhiophosphat (OBETHOAT) O-Aethyl-O-ie-quinolinyH-phenylthiophosphonate (OXINOTHIOPHOS) O-Bethyl-S-methyl-amidothiophoeophate (MONITOR)

0-methyl-0- (2> dichloro-4-broiiphenyl) benzothiophosphonate (PHOSVEL) 0,0,0,0-tetrapropyl dithiopyrophosphate

S-iDiiethoxyphosphinyloxyJ-N-Bethyl-N-iethoxy-cis-crotonanide O.O-Diiethyl-S-iN-äthylcarbanoylnethyDdrthiophosphat (ETHOAT-METHYL) O.O-diethyl-S-iN-isopropylcarbaaoylmethyD-dithiophosphate (PROTHOAT) S-N-d-Cyano-l-EthyUthyDcarbaaoyliiethyldiäihylihiolphosphat (CYANTHOAT) S- (2-Aceta «idoethyl) -0,0-diiethyldithiophosphate Hexauethylphosphorsäuretriaiid (HEUPA)

0,0-Dieethyl-0- (2-chloM-nitrophenyl) thlophosphate (OICAPTHON) 0, Cl-Diaeihy 1 -0-p-cyanopheny) thiophosphate (CYANOX)

O-ethyl-0-p-cyanophenylthiophosphonate O.O-diethyl-O ^ -dichlorophenylthiophosphate (DICHLORFENTHION) O ^^ - Dichlorophenyl-O-methylHsopropylamidothiophosphate O.O-diethyl-O ^ .S-dichloM-broiiphenylthiophosphate (BROKOPHOS-AETHYL) Methyl p- (methyHlo) phenyl phosphate O.C-Dimethyl-O-p-sulfainidophenyl thiophosphate Orfp-ip-chlorophenyl ^ -opheny'jO.O-diiethylihiophosphate (AZOTHOAT) O-ethyl-S-i-chlc-phenyl-ethyldithiophosphonate O-Isobutyl-Spxhlorphenyl-Ethyldithiophosphonat

0,0-diethyl-S-p -chlorophenyl thiophosphate 0,0-D {methyl 1-S- (p-chloropheny11h ionethy1) -d ihiophosphate

O.O-diethyl-p-chlorophenylnercaptoiflethyl-dithiophosphate (CARBOPHENOTHION) OjO-ethyl-S-p-chlorophenylthiomethyl thiophosphate O.O-DJeethyl-S-icarbäthoxy-phenylmethyDdithiophosphat (PHENTHOAT)

0,0-D i äthy1-S- (carbof1uoräthoxy-pheny1methy1) -di thiophosphat 0,0-Diiethyl-S- (carboisopropoxy-phenyI methyl) -dithiophosphate

O.O-OiäthyM-hydroxy-a ^ -tetraaethylene-couiiarinyl-thiophosphate (COUMITHOAT)

2-Bethoxy-4-H-1,3,2-benzodioxaphosphorin-2-s; ilfU 0,0-diethyl-0- (5-phenyl-3-isoQxazolyl) thiophosphate 2- (Diethoxyphosphinylino) -4-Biethy 1-1,3-di thiolane

Tris- (2- «iethyl-l-aziridinyl) -phosphine oxide (BETEPA) S- (2-chloro-1-phthaHbidoethyl) -0,0-diethyldithiophosphate N-hydroxynaphthalimido diethyl phosphate Dinethyl S.S.β-trichloro-4-pyridyl phosphate

0,0-Dinethyl-0- (3,5,6-trichloro-2-pyridyl) thiophosphate

S- 2- (ethylsulfonyl) ethyl diaethylthiol phosphate (DIOXYDEMETON-S-METHYL) Diethyl-S- 2- (ethyl sulfine ethyl dithiophosphate (OXYDISULFOTON) Bis-O.O-diethylthiophosphoric anhydride (SULFOTEP) Ethyl-1,3-di (carbonethoxy) -l-propen-2-yl-phosphate Di «ethyl- (2,2,2-trichloro-1-butyroyloxyethyl) phosphonate (BUTONATE)

0,0-DiBethyl-0- (2,2-chloro-1-ethoxy-vinyl) phosphate

Bis (di «ethylaaido) fluorophosphate (DIMEFOX)

3,4-dichlorobenzyl-triphenylphosphonium chloride

D i methy 1 -N-methoxy ne thy 1 carbainoy 1 inethy 1 -d i thi ophosphate (FORMOCARBAM)

0,0-diethyl-0- (2,2-dichloro-1-chloroethoxyvinyl) phosphate 0,0-dimethyl-0- (2,2-dichloro-1-chloroethoxyvinyl) phosphate

O-Ethy1-S, S-di pheny1d i th i oil phosphate

0-Ae thy 1-S-benzy1-pheny1d i thiophosphonate 0,0-diethy1-S-benzy1-thi oil phosphate

2 0 9 3 /> 1/1 1 7

-B-

OO-dimethyl-S-tA-chlorophenylthiomethyldithiophospha * (METHYLCARBOPHENOTHION) 0,0-dimethyl-S- (ethylthioniethyl) dithiophosphate

Diisopropyl isinofluorophosphate (MlPAFOX)

0,0-Dimethyl-S- (roorpholinyl carbamoy I methyl) dithiophosphate (MORPHOTH (ON) Bi smethy1 ami do-pheny1 phosphate

0,0-dimethyl-S- (benzenesulphonyl) di thiophosphate 0,0-0imethyl- (S and 0) -äihy) sulphinylethylthiophosphate 0,0-diethyl-0-4-nitrophenylphosphate triethoxy-isopropoxy-bis (thiophosphinyl) disulphide 2 -Kethoxy-4H-1,3,2-benzodioxaphosphorine-2-oxide okiamethylpyrophosphoramide (SCHRADAN) bis (dimethoxythiophosphinylsulfido) -phenylmethane p / N'-tetramethyldianiidofluorophosphate (DIMEFOX) O-phenyl-0-p-nitrophenyl-phosphonate -Hleiyl-0- (2-chloro-4-tert-butyl-phenyl) -N-methylamidothiophosphate (NARLENE) 0-ethyl-0- (2,4-dichlorophenyl) -phenylthiophosphonate 0,0-diethyl-0- (A -methyJmercapto-3,5-dimethylphenyl) thiophosphate 4, A '-BiS- (O, O-dimethylthiophosphoryloxy) -diphenyl disulfide 0,0-di- (ß-chloroethyl) -0- (3-chloro-4-methyl- Coumariny1 -7) -phosphate S- (1-phthalimidoethy1) -0,0-diethyldithiophosphate 0,0-Di »e% l-0- (3-chlorom-diethyl sulphamylphenyU-thiophosphate 0-methyl-0- (2 -carbisopropoxyphenyl) amidothiophosphate 5- (0 _f 0-diir, ethylphosphoryl) -6-chlo - bicyclc (3.2.0) -hepladiene (l, 5) O-methyl-0- (2-i-propo xycarbonyl -1-methyl vinyl) äthylami dothiophosphat

Nitrophenols i derivatives

4,6-dinitro, 6-methylphenol , Na salt [dinitrocresol] dinitrobutylphenol (2,2 ', 2 "triethanolamine salt) 2 cyclohexyl-4,6-dinitrophenol [Dinex] 2- (1-methylheptyl) -4,6 dinitrophenyl crotonate [dinocap] 2 sec-butyl-4,6-dinitrophenyl-3-methyl-butenoate [binapacryl] 2 sec-butyMjß-dinitrophenyl-cyclopropionate 2 sec-butyl-4,6-dinitrophenyl-isopropyl-carbonate [ Dinobuton]

Different Pyrethrin I. Pyrethrin Il

3-Al lyl ^ -methyM-oxo ^ -cyclopenten-i-yl-chrysanthemumat (Allethrin) 6-chloriperony1-chrysanthemumat (barthrin) 2,4-dinsethy1benzyl-chrysanthemumat (dimethrin) 2,3,4,5- tetrahydrophthal ΐ mi domethy1chrysanthemumat 4-Chl orbcnzyl-4-chlorphcny 1 sulfide [ chlorine surfactant] 6-methyl-2-oxo- 1,3-diethieto- [4,5-b] -quinoxal in [quinontethionate] (l) -3- (2-Furfuryl) -2-niethyl-A-oxocyclopent-2-enyl (l) - (cis + trans) chrysanthemum monocarboxylate [furethrin] 2-pival oy1 -indane-1,3-dione [pindone] N * - (Λ-chi or-2-methylphenyl) -K, N- dimethylformamide in (chlorophenamidine) 4 -chlorobenzyl-4-fluoropheny 1-sitl fid (fluorobenzene) 5,6-dichloro-l -phenoxycarbanyl-2-trif1uomethyl-benzimidazole (Fenozaflor) p'-chlorophenyl-p-chlorobenzene sulfonate (Ovex) p- chlorophenyl-benzenesulfonate (Fenson) p- chloropheny 1-2,4,5-trichloropheny 1sulfön (Tetradifön) p ! -Chlorpheny1-2,4,5-trichlorophenyl sul fid (tetrasul) p-chlorobenzyl-p-chlorphenylsulfid (Chlorbenside) 2-thio-l, 3-dithio o - (5-6) quinoxaline (Thiochinox) prop-2 -ynyl- (4-t-bu tylphenoxy) -cycl ohexy! sulfite (propargil)

2 0 9 fU 1/1 V7

For »amidine

l-Oimethyl-Z-iZ'-irethyt-A'-chlorphenyD-foriianiidin (CHLORPHENAMIDtN) l-Methy1-2- (2'-methyl-4'-chi orpheny l) -foriiiamidin l-methyl-2- (2 ' -methy1 -A'-bromopheny 1) -f orniamidine 1-! fethyl-2- (2 ', 4'-di! nethylphenyl) -foni> apiidin 1-n-butyl ll-methy1-2- (2'-methy 1 -A'-chlorophenyl) -f orir.amidine! -Methyl -l- (2'-roethy l-ή '-chi orani 1 ino-irethylene) 2- (2''- me thy1-A ¹ ' - chlorpheny1) -formamidine 1-n-Buty1-2- (2'-methy1-4'-chlorophenyl-imlno) -pyrrole id in

urea

N ^ -Methyl-A-chlorophynyl-N'.N'-diiTiethyl-thiourea

Carbamates

1 -Naphthy 1 -N-methy 1 carbainate (CARBARYL) 2-Butιny1-4-chlorphenyicarbanat 4-Din: ethylamino-3,5-xyl yl-N-diethyl carbonate A-Diraethylaiiiino-3-tolyl-N-niethylcarbaipat (AMINOCARB) * - «lethy] thio-3,5-xylyl-N-rethylcarbamate (METHIOCARB) 3,4,5-trinethylphenyl-N-methylcarbamate Z-chlorophenyl-N-methylcarbamate (CPMC) S-chloro-B-oxo-Z-norbornane-carbonitrile-O-imethylcarbamoyn-oxime ! - (Dirae-thylcarbamoyO-S-methyl-S-pyrazolyl-N ^ -dimethylcarbamate (DIMETlLAN) 2,3-Dihy {fro-2,2-diinethyl-7-benzofuranyl-N-! -Nethylcarbaniate (CARBOFURAN) 2-Hethyl-2-methylthio-propϊona1dehyd-0- (methyl carbamoy1) -oxime (ALDICARB) 8-quinaldyl-N-methylcarbaiate and its salts Methyl 2-isopropy1-A- (methy1carbamoy1 oxy) carbanilate n- (1-ethylpropyl-phenyl-N-methylcarbamate 3,5-di-tert-butyl-N-methylcarbamate

B- (I-methyl butyl) pheny1-N-ethyl carbanate

2-isopropyl phenyl-N-methyl carbamate 2-sec.Bu ty 1 phenyl-N-methylcarbamate ( ro-toly) -N-methylcarbamate 2,3-xy1y1-N-methylcarbamate 3-isopropylphenyl-N-methylcarbamate 3-tert-butylphenyl -N-methylcarbamate 3-sec-butyl phenyl-N-methylcarbamate 3-isopropy1-5-methy1pheny1-N-methy1carbamate (PROMECARB) 3,5-D i ΐ sopropy1 phenyl-H-methy 1carbamai 2-chloro-5- isopropylpheny1-N-methylcarbamate 2-ChloM, 5-dimethylphenyl -N-methylcarbamate 2- (1,3-diaxolan-2-yl) phenyl-N-methylcarbanate (DIOXACARB) 2- (A, 5-D1ir.ethyl -!, 3-dkxolan-2-vl bh ^ vl-V ^ + Hylcarbauiat 2- (i, 3-Dijxolan-2-yl) phenyl-N, N-dimethytcarban! St 2- (1,3-DHhiol3r-2 -yt ^ ", M-dimethylcarbamate 2- {1,3-dithiolar-2-yl) pre'-yi-N, N-diii; etu / ltarbai! iat 2-liopropoxyphenyl-N-bisethylcarbatate (ARPROCARB) 2- ( 2-Propinyloxy) phenyl-NB \ ethylcarban'at 3- (2-Prop ϊ ny1 oxy) pheny1-N-methylcarbamate 2-Diniethylaninophenyl-N-rethy lcarbamat 2-Diallylanlriophepyi-N-irethylcarbara + ♦ -OiaHylair.ino-a ^ .ino-a ^ .ino-a ^ -xylyl-K-ire'hyicarbanat (ALLYXICARB) A-Benzothienyl-N-methyIcarbanat 2,3-Di hydro -? - inethyl-7-benzofuranyl-N-methylcarbaroate S-diethyl-1-phenylpyrazol-S-yl-NjN-dkethylcarbaniat 1-isopropy 1 -3-ire thy lpyia / ol-5-yl -N, N-dine Thy lcarbamat (ISOLAN) 2-Dimethy 1 am ino-5, G-diethyl pyrimidin-4-yl-N, fl-d imethyl -cartamat

2 O 9 B A 1/1 1 7

-i -. 'i'ciiiy l-'t-ilisnliiyl.'iiniiKisicihy leu i r; i inopher.yt-W-πυ · lhytcarbamat 3, Ί-D i me t hy 1 phcny 1 -N-ni thy IcartMma t 2-Cyc I open Iy I pheny IN-me thy I ca rb; j «ia t 3 - [) imethy] nmino-melhy 1 eniminophcny 1-N-motliylrarbamat (FORMETANATE) and its salts 1-MethyIIhio-äthylimino-N- mcthy! carbjmjt (Mi.HIOMYL) 2 — Mo tisy i c <irhamoy 1 ox im ino — 1,3-di ihiolan 5-Mo t hy 1 —2 — mc thy lcarbamoyl ox im ino-1,3-oxy thiolan 2- (1-Mc thoxy-2-propoxy) phcny 1 -N-me iliy] carl> nna t ? - (I-Hu ti HJy I-oxy) phcny 1-N-diii I hv 1 r, i γΙι, ίπμ t

I -Il i im thy 1 cirbamy I -1 -me thy I th i o-Ü-ice ihy 1 carbamy 1 -f ormox im

] - (2'-Cyanoethy 1thio) -0-methylcarbamy1-acetaldoxime 1 -Me thy Hh i o-0-carbamy 1 -ace ta 1 dox i m 0- (3-sec-butyl phenyl) -N-phenylthio-N-methylcarbamate 2,5-Πiraethy 1-1,3-dithioland-2- (0-methy 1 carbaray 1) -aldoxime) 0-2-Di pheny1-N-me thy 1carbama t

2- (N-Me "thy lcarbamyl-oximino) -3-chlor-bicyclo [2.2.1] heptane 2- (N-MethyIcarbamy1-oximino) bicyclo [2.2.1Jheptane 3-1xopropy1pheny1-N-methy1-N-c h1orac e ty 1-carbama t 3-Isopropylpheny1-N-methy 1-Ν-methy 1-thiomethyl 1-carbamate 0 - (?, 2-dimethyl-4-chloro-2,3-dihydro-7-t> enzofuranyl) -N-methylcarbamate 0- (2,2, "- Triraethy I2,3-dihydro-7-benzofuranyl) -N-methylcarbamate

O-naphthy1-N-methyl-N-acety1-carbamate

0-5,6,7,8-tetrahydronaphthyl-N-iuethyl-carbainate 3-Isopropyl-4-methylthiophenyl-N-methylcarbamate 3,5-D i me thy 1 -4-methoxy-pheny 1 -N-me thy 1 carbania t 3-methoxymethoxyphenyl-N-methylcarbamate 3-Λ11y1oxypheny1-N-methy1carbama t 2-IVoparqy 1 oxyrac t hoxy-phcny 1 -N- ^ no thy 5 -carhama t 2-Λ1 lyloxyplienyl-N-mcliiyl-c.'ii'lianiut Ί-Me Ihoxycarbony 1 nmitio-3-ir, opro |) y I phenyl-N-me t hy l-carbamate j / J-Dimethyl - ^ - methoxycarbonylaniinn-pheityl-N-diethyl-carbamate 2-y-methyl 1-th iopropylpheny 1-N-methyl 1-carbamate 3- (a-Me thoxyrae thy 1-2-propcny1! -Phenyl-N-methy1-carbamate 2- Ch1or-5-1ert-buty 1-pheny1-N-me thy 1-ca rbama t ^ - (Methyl-proparqy taoiino) -3,5-xylyl-N-methyl-carbama t Ί- (MethyΙ-γ-chloralylamino) -3,5-xyly) -N-methy1-carbamate

A- (Me thy1-ß-chloroalylamino) -3,5-xylyl-N-methyl-carbaroate

1- (ß-ethoxycarbonylethyl) -3-niethyl-5-pyrazotyl-N, N-diniethy 1-carbamate 3-Methy 1-4 (dimethylamino-methy 1 mereapto-methyleninino) phenyl-N-methy1carbamate l ^ -nisfcarharaoylthioJ ^ -iN.N-dimethylaminoJ-propane hydrochloride 5.5, Π i me thy 1hydroresorc inold i mothy 1carbama t ? - \ he thy l-propargylaninoj-phenyl -N-me thy 1 carbama t .'- [Methyl-propargylaeino] -pheny] -N-methy 1 carba mat 2- [Dipropargylaiino] phenyl-N-methylcarbanate 4- [propargylanino] -3-tolyl-N-methylcarbanate

A- [propropargyla »ino] 3,5-xylyl-N-methylcarbamate

2- [Alyl-isopropyl-1no] -phenyl-N-methylcarbamate 3- [A1] y] isopropy] amino] phenyl N -methyl carbamate

2202A7 1

2098A1 / 1172

2202A71

Chlorinated carbonic solids Y-llexachlorocyclohexane [GAMMfXANL ';LINDAN; γ HCH]

[CHLORDAN]

O, 3α, '(, V ^ a-tetrahydro-i ^ -methyleneindan [HEPTACHLORJ 1. ". J, A, 10, lO-l-.exachlor-l, 4, 'ia, 5,8,8a-hexahydro-endo-1,4-exo-5,8-dime1: hanonaphthalene [ALDRIN]

[DIELDRIL [[NCRIu]

2 O S CU 1/1 1 7 2

In addition, the compounds of the formula I have no- ticidal properties and can, for example, be used to control the following plant-parasitic nematodes: Meloidogyne spp., Heterodera spp., Ditylenchus spp., Pratylenchus spp., Paraty 1 rnehus spp., Anguina spp. , Helicotylencnus spp., Tylenchorhynchus spp., Rotylenchulus spp., Tylenchulus semipenetrsns, Radcpholis sinnJus, BelonolalsiTius spp. , Trichodorus spp. , Longldorus spp. , ApbeJenchoides spp., Xiphinema spp ..

2 0 9 iU 1/1 1 7 2

The compounds of the formula I can be used alone or used together with suitable carriers and / or aggregates will. Suitable carriers and aggregates can be solid or be liquid and according to those in the formulation technique Usual substances such as natural or regenerated substances, solution, dispersing, wetting, adhesive, thickening, binding and / or Dough.

The compounds of the formula (I) can be used for administration Dusts, emulsion concentrates, granules, dispersions, sprays, to solutions or slurries in the usual formulation which are part of general knowledge in application technology. Furthermore, "cattle dips", i.e. cattle baths, and Mention should be made of "spray races", i.e. spray courses in which aqueous preparations are used.

The agents according to the invention are produced in and of themselves known way by intimate mixing and / or grinding of Active ingredients of the formula I with the suitable carriers, if appropriate with the addition of dispersants or solvents which are inert towards the active ingredients, the active ingredients can be used in the the following processing forms are available and used:

solid processing forms: dusts, grit,

Granulates, coating granulates, Impregnation granules and homogeneous granules

■ liquid coloring forms:

a) dispersible in water

Active ingredient concentrates: wettable powder,

Pastes, emulsions;

b) Solutions

For the production of solid processing forms (dust, Litter) the active ingredients are mixed with solid carriers. Carriers include kaolin, talc, bolus, loess, chalk, limestone, lime grit, ataclay, dolomite, diatomaceous earth, Precipitated silica, alkaline earth silicates, sodium and potassium aluminum silicates (feldspars and mica), calcium and magnesium oxide, ground Plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, urea, ground vegetable products,

'209 841/1172

such as grain flour, tree bark flour, wood flour, nutshell flour, Cellulose powder, residues from plant extractions, activated charcoal etc., each on their own or as mixtures with one another iti question.

Granules can be produced very easily by adding an active ingredient of the formula I in an organic solvent dissolves and applies the resulting solution to a granulated mineral, e.g. attapulgite, SiCL, granicalcium, bentonite, etc. and then the organic solvent is evaporated again.

It can also be used to produce polymer granules. that the active ingredients of the formula I are mixed with polymerizable compounds (urea / formaldehyde; dicyandiamide / formaldehyde; melamine / formaldehyde or others), whereupon a gentle polymerization is carried out, which does not affect the active ingredients, and granulation is carried out while the gel is being formed will. It is cheaper to impregnate finished, porous polymer granules (urea / formaldehyde, polyacrylonitrile, polyester and others) with a certain surface area and a favorable, predeterminable adsorption / desorption ratio with the: active ingredients, e.g. in the form of their solutions (in a low-boiling solvent) ζυ and remove the solvent. Such polymer granules can also be applied in the form of micro-granules with a bulk density of preferably 300 g / liter to 600 g / liter with the aid of atomizers. The atomization can be carried out over large areas of crops of useful plants with the help of airplanes.

Granules are also available by contacting the carrier material with the active ingredients and additives and then crushing available.

These mixtures can also contain additives stabilizing the active ingredient and / or nonionic, anionic and cationic active substances. Fabrics can be added, which, for example, improve the adhesive strength of the active ingredients on plants and parts of plants (adhesives and adhesives) and / or ensure better wettability (wetting agents) and dispersibility (dispersants).

For example, the following can be considered: olein lime mixture, Cellulose derivatives (methyl cellulose, carboxymethyl cellulose), hydroxyethylene glycol ethers of mono- and dialkylphenols with 5-15 Ethylene oxide residues per molecule and 8-9 carbon atoms in the alkyl

209841/1172

remainder, lignin, eulphonic acid, its alkali and alkaline earth salts, I-olyethyl englyco] ethers (carbowax). rettalkoholpolyglykoläther ηύΐ. 5-20 Aethylenoxidresten per molecule, and 8-13 carbon atoms in the fatty alcohol part, condensation products of Aelhylertoxid, Propylenoxi ο, polyvinylpyrrolidones, Pol ^7} vinyl alcohols, condensate ionsprο ■ -dukte of urea / formaldehyde and latex products.

Active ingredient concentrates dispersible in water, i.e. wettable powders (wettable powder), pastes and emulsion concentrates st '. Ilen Means which can be diluted with water to any concentration can be. They consist of active ingredient, carrier., If necessary additives stabilizing the active ingredient; surface-active Substances and antifoams and, if necessary, solvents.

The wettable powders and pastes are obtained by inan the active ingredients mi! Dispersants and powders Carriers in suitable devices until they are homogeneous mixed and married. As dreams come for example those mentioned above for the fixed arbel forms in days. In some cases it is advantageous to use mixtures of different Use carriers. As di .spergntoren can, for example used x; earth: reaction product of sulfonated Naphthalene and sulfonated naphthalene derivatives with formaldehyde, Condensation ationspi-'odukire des naphthalins or naphthalenesulfonic acids with phenol and formaldehyde as well as alkali, AitVionium and Alkaline earth salts of ligninsulphonic acid, further alkylaryli vüfonale. Alkali and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, Fatty alcohol sulfates, such as salts of sulfated hexadecanols, heptodecano] s, Octadecanols and salts of sulfated fatty alcohol glycol ethers, the sodium salt of oleyl methyl tauride, ditertiary ethylene glycols, Dialkyldilaurylammonium chloride, and fatty alkali and alkaline potassium salts.

Silicone oils can be used as antifoam agents in the example.

The active ingredients are mixed with the additives listed above, ground, sieved and happens that with the spray powder at the front the solid portion does not exceed a grain size of 0.02 to 0.04 and in the case of the pastes does not exceed 0.03 mm. For production of Emulsion concentrates and pastes are dispersants as listed in the previous sections, organic Solvent and water used. Both solvents

209841/1172

for example alcohol, benzene, xylenes, toluene, dimethy] sul fox ic] vvö in the range from 12 ° to 35O "C dedende mineral oil fractions in Fry ge. The solvents have to be odorless, not phytotoxic and inert to the active ingredients.

Furthermore, the agents according to the invention can be in the form of solutions be sent. For this purpose, the active ingredient or several active ingredients of the general formula 1 are used in suitable organic Solvents, solvent mixtures or water. Aliphatic and aromatic hydrocarbons, their chlorinated derivatives, alkyl naphtha] ine, Mineral oils used alone or as a mixture with one another: are.

The content of active ingredient in the agents described above is between 0.1 and 95%, it should be mentioned that in the Application from the aircraft or by means of other suitable application devices Concentrations up to 99.5% or even more pure Active ingredient can be used.

The active ingredients of formula T can be formulated as follows, for example:

Dust: For the production of a) 5% and b) 2% dust the following substances are used:

a) 5 Parts Active ingredient 95 Parts Talc; b) 2 Parts Active ingredient "

1 part of highly disperse silica, 97 parts of talc

The active ingredients are mixed with the carriers and marry.

Granulate: The following substances are used _{to produce 57 c igen granulate:}

5 parts of active ingredient
0.25 part of epichlorohydrin,
0.25 part of cetyl polyglycol ether, 3.50 parts of polyethylene glycol
91 parts of kaolin (grain size 0.3-0.8 mm). /

The active ingredient is mixed with epichlorohydrin and '"

dissolved with 6 parts of acetone, then polyethylene glycol and

209341/1172

Cetyl polyglycol ether added. The solution obtained in this way is sprayed onto kaolin and then the acetone is evaporated in vacuo. Wettable powders: Ζ · .η: Preparation of a) AO 7> strength _s b) and c) 25 7oigen d) 10 days, the wettable powder v / ground following Rebtandteile used:

a) 40 parts of active ingredient

5 parts of Llgnlsulfonsfiure-sodium salt, 1 part dibutyl naphthalenesulfonic acids Natriuinsi'l z> 54 parts of silica;

b) 25 parts of active ingredient

4.5 parts calcium lignin sulfonate,

1, 9 parts of Chanipagne chalk / hydroxyethyl cellulose

Geinisch (I;]),

1.5 parts of sodium dibutyl naphthalene sulfonate,

19.5 parts of silica,

19.5 parts of champagne chalk,

28.1 parts of kaolin;

c) 25 parts of active ingredient

2.5 parts of isooctylphenoxy polyoxy methyl en- «thand, 1.7 parts champagne chalk / hydroxyethyl cellulose

Mixture (1: 1),
8.3 parts sodium aluminum silicate,

16.5 parts kieselguhr,

46 parts of kaolin;

d) 10 parts of active ingredient

3 parts mixture of the sodium salts of saturated

Fatty alcohol sulfates,

5 parts of naphtha] insulphonic acid formaldehyde condensate, 82 parts of kaolin.

The active ingredients are intimately mixed with the additives in suitable mixers and ground on appropriate mills and rollers. Wettable powders are obtained which can be diluted with water to form suspensions of any desired concentration. Emulsifiable concentrates: The following substances are used to produce a) 107o and b) 257 _{c emulsifier concentrate:}

2 0 ^ 41/1172

a) 10 parts of active ingredient

3.4 parts epoxidized vegetable oil,

13.4 parts of a combination emulsifier, consisting of Fatty alcohol polyglycol ethers and alkyl aryl sulfate calcium salt,

40 parts of dimethylformamide, 43.2 parts of xylene; 25 parts of active ingredient

2.5 parts epoxidized vegetable oil,

10 parts of an alkylarylsulfonate / fatty alcohol poly-

glycol ether mixture, 5 parts dimethylformamide ..

57.5 parts of xylene.

Emulsions of any desired concentration can be prepared from these concentrates by diluting them with water. Sprlihmittel: 7 to produce a 5 _cent, spraying agent the following components grazing used:

5 parts of active ingredient, 1 part of epichlorohydrin, 94 parts of gasoline (boiling limits 160 ° -19O ° C);

209341/1172

Example 1

63.5 g of 1-] sopropyl-3-hydroxy-1,2,4-triazole and 69 g of potassium Carbonate in 1500 ml of methyl ethyl ketone are on for one hour RUckfJuss heated.

After cooling to room temperature, 54 g of dimethyl carbamyl chloride in 100 ml of methyl ethyl ketone are added dropwise. The loting is heated to the boil for a further 2 hours. After cooling, the salts are filtered off and the filtrate is concentrated. The liquid residue is taken up in methanol uid in the carbon dioxide / acetone bath cooled to -70 ⁰ C. The excreted, crystalline active ingredient of the formula

CH - Ν - —N O V ¹ N CH ₀ I. if Il / 3 I. • I -C- 5 HC C - - O

is filtered off and dried in vacuo (40 ° C./15 mm Hg) for 6 hours. The following connections are established in an analogous manner:

209841/1172

links

■ Ν, N-Diinethylcarbanioy 1 - f l-ethyl -1,2, 4-t: riazolyl · - (3)] -ester N, N-dimethyl cn rbamoyl - f] .- n-propyl - 1,2 , 4-triazolyl- (3)] - ester Ν, Ν-dimethylcarbarnoyl- 11- isopropyl -1, 2, 4-triazolyl- (3)] - ester N, N - diniethylcarbamoyl - [1-n-butyl -1, 2, 4-trϊη-zolyl- (3) ] -ester N, N-dimethylcarbanioyl- [1-scc-butyl-1,2,4-trίazolyl- (3)] -ester NN-Üiinethylcarbar. ioyl- [1-isobutyl-l, 2, 4-triazolyl (3)] - ester N, N-Dimethylcarbr.Ti.Oyl- [1- lake. -peuty 1 -1,2,4-tri.ayoly 1 - (3)] -cater NiN-Dimethylcfirbaiioyl- [1-n-hexyl-1,2,4 - <: r I azo] yl- (3)] -ester Ν, Ν-Diniethylcarbamoyl - [1 -cycloponty 1 -1. 2,4-triazolyl- (3)] - ester N, N-Dinietbylcarbavnoyl- [l-ai: hy] -5-nicthy] -1, 2,4-triazoly1- (3)] - ester N, N -Di methylcarbamoyl- [1-isopropy] -5-methy 1-1,2,4-triazoly] - (3)] - ester N, N - dimethylcarbamoyl- [1-isopropyl-5-ethoxycarbony 1,2 , 4-triazoly] - (3) 1-ester Ν, Ν-diethylcarbamoyl- [1-isopropyl-1,2,4-triazolyl- (3)] - ester Ν, Ν-dimethylcarbainoyl- [1- (1 ', 2 ', 2' -trimethylpropyl) -1,2,4-triazolyl- (3)] -ester N, N-dimethylcarbamoyl- [1- (1'-ethy] propyl) -1,2,4-triazolyl- ( 3) 1-ester N, N-Diiiiethylcarbamoyl- [1-isopropyl-5-ethy] -1, 2,4-iriazoly] -C3)] - ester N, -Methyl-N-methoxycarbamoyl- (1-isopropyl -1,2,4-triazolyl- (3)] - ester N, N-Di meihy1carbamoy1- [1-is opropy1-5 -cy anο-1,2,4- tria 7. Öl yl- (3 ) ) -e ε t. egg:

TTT

Pp .: 57-6B "C.

Fp ;; 55-5 8 ° C

Mp .: 76-77 ⁰ C

M.p .: 31-35 ° C

M.p .; 44-33 'C

i .: 71-73 "c:

M.p .: 33-37 "C.

M.p .: 36-38 ° C

²⁰ x 1 49C9

Mp .: 10S-110 ^c

Fp .:

20 ^Ί ϋ ^:

Φ ·:
Fp .:
Fp .:
Fp .:

64 ° C 1.4721 97-100 ° C 58-6O ° C P.3-8VC 62-65 ^c 'C

- .21

links

Ν, Ν-methylcarbamoyl- [l-sec-pent: yl-l, 2, 4-tri-azolyl- (3) I-ester

N.N-Diitiethylcarbamoyl - [1, ii-diisoproß ?! -1, 2, 4-triazolyl- (3)] - ester

20 D

0 9 8 4 1/117

At game 2
Λ) Insecticidal milling ν. gi ft effect

Tobacco and potato plants were puffed with a 0.05 aqueous active ingredient emulsion (obtained from a 10 7oigen emulsifiable Concentrate).

After the coating had dried on, the tobacco plants were populated with owl owls (Spodoptera litoralis) and the potato plants with Colorado beetle larvae (Leptinotarsa decemlineata). The experiment was carried out at 24 ° C and 60 _O 7 relative humidity.

The compounds according to Example 1 showed in the above test Food poison effect against Spodoptera litoralis and Leptinotarsa decemlineata.

V. ) S ysteir. i sch-insecticidal effect

To determine the systemic effect, rooted bean plants (Vicia faba) were placed in a 0.01 7dge aqueous active ingredient solution (obtained from a 10% emulsifiable concentrate). After 24 hours, aphids (Aphis fabae) were placed on the above-ground parts of the plant. The eggs would be protected from contact and gas effects by a special device. The experiment was carried out at 24 ° C. and 70% relative humidity.

The compounds according to Example 1 acted systemically against Aphis fabae in the above test.

C) Insecticidal control toxicity

Acetonic active ingredient solutions were converted into Petri dishes

2 active ingredient coatings of 0.15 g active ingredient per inch were applied. After one hour the shells were populated with house flies (Musca dornestica). The compounds according to Example 1 showed contact poison activity against Musaca dornestica in the text above.

209841/1172

Example 3

W Irku ng g ay B od o nn em? weary

To test the effect against soil antennas, the Active ingredient at a concentration of 50 ppm in by Wnr: -. Ej-gallen nematodes (Meloidogyne Avenarla) given infected soil and intimately mixed. In the earth prepared in this way were in one Test series planted tomato scuttles immediately afterwards and in another series of experiments torrinter waiting time n «c-li P days sown seeds.

To assess the nematozidc-n \ v ^T : I_kung 28 days: after planting bzv7. after sowing the galls present on the roots are counted. The compounds according to Example 1 showed a nematocidal effect in a cbigen test.

2 0 9 Π A1 / 117 2

Claims (1)

Pat for rm / rprlic ! ■ _, connections of the form ¹ ! R ₁ - N ~ N ¹ I Il ο Il R ₀ -Q COCN ^ NNN P R ₄ wherein R, hydrogen, alkyl or cycloalkyl, R "hydrogen, alkyl or the groups -COOK-, -CO-N (R ₃ ) (R ^) or -CN, R ₃ hydrogen, alkyl, alkenyl or alkynyl, R _f AlUyI . Alkenyl, AlWhyl, alkoxy, cycloalkyl or phenyl and R ~ and R, together with the nitrogen atom to which they are attached, represent a heterocyclic radical. 2. Compounds according to claim 1 of the formula ^R 8 wherein R _{5 is} hydrogen, C, -Cg alkyl, or C ₃ -Cr cycloalkyl, R, hydrogen, C ₁ -C ₄ alkyl or the groups -COOR ₅ , -CO-N (R-,) (Rg) * R ^ Hydrogen or C 1 -C, alkyl and R _g denote C 1 -C, alkyl, C. -C 4 alkoxy or phenyl. 3. Compounds according to claim 2 of the formula ^S l ~~ \ f ° / - ^R n R _1n -C CO-C-N ^N ρ ^R 12 wherein R _{9 is} C 1 -C 4 alkyl, cyclopentyl or cyclohexyl, R _{1 is} hydrogen; C ₁ -C, alkyl or the groups -COOCH. ,, -COOC ₀ Ht- or -CON ³ 209841/1172 ! Ι ... hydrogen, methyl or Ac; thy J. and R
Methiv-.y or phenyl mean. Methyl, ethy. I. Connection goinasi; Claim 3 of the Foiuiel CIU ^ ^J ^ - CH - NW CH, HC O - C-N vN- CII ₃ CIL A compound according to claim 3 of the formula HoC ₂ - NN lid Nn / Il C-N Compound according to claim 3 of the formula CII. CIL CH CH, C O - C - N ^jn 3 A compound according to claim 3 of the formula N N II] HC C- »
OCN CLL 209841/1172 8. Procedure for making the connections of the Γοπί-ο! ~ ^MW 0 ^ R ^ Il ^ - · R ₀ - C COCN ^R 4 ■ wherein R is hydrogen, alkyl or cycloalkyl. R "Hydrogen, Alky! or the groups -COOR- ,, -CO-N (R ₃ ) (R.) or -CN, R ₃ hydrogen ⁷ , alkyl, alkenyl or alkynyl, R, alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl or phenyl and R ₃ and R ^ together with the nitrogen atom to which they are attached represent a heterocyclic radical, characterized in that moη is a Hydroxytriazoi Her formula R \\ μ ¹ j ι R ₂ -U C - OH wherein R, and R "have the meaning given above with one: Carbauiyl halide of the formula 0 .Ro Il s' J Shark - C - N ¹ M. where R- and R, before the meaning given above and Hal F, Cl, Br or I means, reacts in the presence of an acid-binding agent. 9. Pesticides which, as the active component, are a compound of the formula - N - - N 0 - 0
Il N 1 I. Ii C - R ₂ -C ρ - wherein R. ^ is hydrogen, alkyl, or cycloalkyl, R _{2 is} hydrogen, alkyl -CO-H (R ₃ ) (R,) ( 2098Af / 1172 or the groups -COOR., -CO-H (R ₃ ) (R,) or -CN, R ₃ hydrogen, 1/1 1ΪΤ Tl - Alkyl, alkenyl or alkynyl, R ₄ alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl or phenyl and R ^ and R, together with the nitrogen al oui to which they are attached, a heterocyclic radical; t and suitable carriers and / or contain other additives. 10. Use of a compound of the formula r '- N N ^ I Il ?. ^ ³ R ₀ -C COCN where R ^ is hydrogen, alkyl, or cycloalkyl, R _{0 is} hydrogen, alkyl or the groups -COOR ₃ , -CO-NOl ₃ ^ (H ₆ ) or -CF, R _{3 is} hydrogen, alkyl, alkenyl or alkynyl, R, alkyl, Alkenyl, alkynyl, alkoxy, cycloalkyl or phenyl and R “and R ^,; αι; · .amines with the nitrogen atom to which they are bonded represent a heterocyclic radical for combating various plant and animal pests. 11. Use according to claim 10 for combating insects. 12. Use according to claim 10 for combating plant parasites Nematodes. 209841/1172